The Princess and the Pirate is a 1944 farce comedy starring Bob Hope. The Princess Margaret (played by the absurdly gorgeous Virginia Mayo) is on a ship bound for America, traveling incognito. She is fleeing from her father the King, who is forcing her into an Arranged Marriage instead of letting her marry the commoner she loves. Also on board is Sylvester the Great (Hope), a bumbling Large Ham actor. The ship is raided by pirates, and both Margaret and Sylvester are captured, but they escape with the help of Featherhead (Walter Brennan), the ship's Butt Monkey, who also provides them with a map to the treasure that Featherhead wants to steal.

This film contains examples of:

The Cameo: Bing Crosby, Hope's co-star in the Road to ... pictures, shows up at the end as the commoner that Princess Margaret is in love with. This was a gag taken from the Road movies, when it was always Bing and never Bob that wound up with Dorothy Lamour.

Sylvester: I work my brains out for nine reels, and some bit player from Paramount comes over and steals my girl. That's the last picture I'll ever make for Goldwyn!

Lovable Coward: Sylvester is a self-admitted coward, but in the end he does go to great lengths to save Margaret.

MacGuffin: The treasure, and the treasure map. They never even look for it. The film ends with the King rescuing Margaret and Sylvester and offhandedly mentioning that one of the bad guys told him where to find the treasure.

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